


A Pleasing Land of Drowsy Head

by chewysugar



Category: Supernatural
Genre: Banter, Blow Jobs, Come Swallowing, Deepthroating, Fluff and Crack, Forests, Ghosts, M/M, Public Blow Jobs, Public Sex, Sex in/on the Impala (Supernatural), Sleepy Hollow - Freeform, The Legend of Sleepy Hollow - Freeform, Voyeurism, Wincest - Freeform
Language: English
Status: Completed
Published: 2019-04-07
Updated: 2019-04-07
Packaged: 2020-01-06 01:06:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,493
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18377816
Author URL: https://archiveofourown.org/users/chewysugar/pseuds/chewysugar
Summary: Turns out, the Headless Horseman is kind of a pervert.





	A Pleasing Land of Drowsy Head

**Author's Note:**

> Title taken from the poem "Castle of Indolence" found at the beginning of the book "The Legend of Sleepy Hollow." 
> 
> Was going to wait til Halloween for this, but I'm impatient.

Ordinarily, a hot mouth around his penis would prevent Dean from thinking of anything else besides pleasure. But at the moment, all he could think of was the irony of the situation.

He looked down at Sam's bobbing head. “You had this planned, didn’t you?”

Sam looked up, his lips and chin shining with spit. Dean’s cock slipped from his mouth, and Dean hissed at the loss of the tight warmth.

“Would you rather have fucked a pumpkin?”

“No. And don’t get slack on me.” He took Sam by the back of the head, guiding him back to his gradually shrinking erection which, once safely ensconced in Sam’s throat, returned to Dean’s preferred state of magnificent tumescence.

He sighed, and leaned back on the hood of the Impala. His jeans were open, but the air had proven too chill for going completely bare below the waist. A pity, as Dean could have gone for some ass action along with the blow job.

Looking around at the autumnal scene around him, Dean felt especially perverted. They’d parked under trees that looked as if they’d walked out of a Grandma Moses folk painting of Colonial America. Leaves of red, orange and yellow spiraled earthwards, carried by the night breeze.

“You had to have planned this,” Dean went on, savoring the sight of Sam slobbering over his knob, “ ‘cause only you’d have seen the irony in giving me head in Sleepy Hollow.”

Having already been scolded for not talking with his mouth full, Sam only hummed in response. Dean’s hips bucked reflexively, his cockhead brushing against Sam’s tonsils.

“Steady there, Gunpowder,” Dean breathed. “I wanna last for the bragging rights.”

At that, Sam had to come back up for air. He seemed to decide that Dean Junior needed warmth above all else, and so contented himself with jerking Dean off.

“Gunpowder was the horse in the story,” Sam said. “He was old and broken down—

“But with a bit of the Devil in him.” Dean smirked at Sam’s evident surprise. “You used to read it to me every Halloween.”

Sam chuckled. “And you remembered.”

“ ‘Course I remembered, Sammy.” He wouldn’t say what he really thought--that he'd have been the worst kind of bastard to ever forgot those warm, fuzzy memories. It would be too wrong in the midst of this weird porno they’d entered into.

Sam’s tongue lapped at the crease in Dean’s nuts. Dean shuddered, curling his fingers into fists.

“Too bad this turned out to be a bust,” he sighed. Then, he plunged Dean’s cock back into his mouth—past the softness of his tonsils and down until it bumped against the back of his throat.

Dean jumped; and Sam’s throat contracted at the sudden movement. But Sam was nothing if not a master of his craft. He breathed through his nose, each exhalation tickling at the hairs of Dean’s groin.

“Keep that up,” Dean said through clenched teeth, “and this hunt won’t be the only bust.”

They’d been driving in the complete opposite direction of New York State when Sam had hit upon the news story. It had occurred to them how strange it was that they’d never been to one of the most famously haunted spots in the country in all their lives.

But a week of searching, sight-seeing and screwing had turned up nothing. What they’d thought would turn into a sighting of the famed Dullahan had ended up with a more mundane solution: a crazed stripper with a vendetta against an ex-boyfriend had been cutting off the heads of those closest to him. Under the guise of Irving’s legend, the chase had taken on an almost fable-esque quality. Then the truth had come out, and both Sam and Dean had developed a jones to disappear.

But Sam had wanted to wait just a little longer—just to see. Dean had never been able to resist that eager, little kid excitement that always lit up his brother’s eyes whenever he truly looked forward to something.

The blowjob had been a joke. A quid pro quo in exchange for lingering in what, to Dean, was nothing more than a historical tourist trap.

As evident by how enthusiastically Sam was going down on him, he’d taken up the challenge. Dean wasn’t so sure it hadn’t been poetic irony, either.

“Would’ve been...nice to see it, though,” Dean gasped. Fuck a donut, but he was getting close. “Just to...see if it was...real.”

He looked around at the woods once more.

Dean frowned. A patch of fog had drifted behind the branches of a massive oak tree some two hundred yards off.

At least, it looked like a patch of fog.

The clouds chose that moment to shift; the light of a full moon illuminated the woods in its silver glow.

Dean’s jaw dropped. Then his eyes rolled back into his head as Sam’s deft fingers slid between his balls and teased at his skin.

“Sammy,” Dean gasped. But he couldn’t formulate coherent words, and he’d be insane to want Sam to stop now of all times.

Not even to stare properly at the ghostly apparition possibly watching them from between the branches.

Dean could only guess as to where the thing looked because it didn’t have eyes. For that matter, it didn’t have a head. But the face of the silvery steed it sat upon pointed in their direction so steadfastly that Dean refused to believe it was looking anywhere else.

“Holy shit,” Dean gasped. He should have been completely turned off, but he couldn’t control the galloping hooves of his libido. In any case, the Horseman didn’t appear to want anything more or less than to sit and watch.

And indeed, the ghost leaned forward on its saddle—peering for a closer look.

“Oh fuck.” Dean thrust upward once into the heat of Sam’s mouth. His nuts throbbed as he spurted ropes of hot load down his brother’s gullet. He gripped Sam’s hair, still staring at the observant phantom. Sam swallowed every last salty volume of Dean’s semen, but now that the moment had passed, Dean had other things on his brain.

“Sammy,” he gasped, tugging Sam’s head away. “Look!”

“Wha?” Cheeks red, lips stained with come, Sam turned his face towards the tree. His eyes went wide, and he scrambled up onto Baby’s hood.

The Horseman’s body tilted to the side. His cape, and his horse’s wild mane and tail, stirred in a constant state of motion, as if a stronger wind than that which tickled the trees blew them.

Dean registered that sitting on top of a car with his dick out, freshly sucked off by his little brother, wasn’t exactly a respectable way to make the acquaintance of such a legendary spook. But he couldn’t move. Hell, he couldn’t even find it in him to be scared. Certainly, the Horseman didn’t seem as if were bound to leap upon them and lob off their heads.

Then the specter stretched back in his saddle. A laugh split the silent October night, one that made Sam jolt closer to his brother. The Hessian’s laughter shook the leaves from the trees overhead, and chilled the air just that much more. But still, it wasn’t entirely frightening. Not meant to menace, but to enjoy. Dean recalled the laughter he'd overheard at various bars around the country--when the more mischievous dudes found something truly amusing

The Horseman jerked the reins of his steed to the side. With a shrill whinny, the phantom horse tossed its head, and galloped towards the West. Just before both horse and headless rider vanished in a flash of dead, white light, the Hessian let peal another laugh.

Sam and Dean sat motionless, wondering if their ghostly visitor would return. It was only when the caress of the night air against his bared groin caused him some embarrassing shrinkage that Dean came back to earth.

He tucked his cock back into his briefs, and zipped his up fly.

“That was...” Sam’s voice trailed away. He looked completely dumbfounded, which Dean found somewhat adorable.

“Yeah,” Dean held a hand out, and helped his brother off Baby’s hood. “That definitely brings literature closer to a person.”

“Do you think he’s...y'know...also missing his _other_ head?”

Dean’s laughter could have put that of the Hessian to shame.

“You can’t blow ectoplasm, Sam.”

“Are you speaking from experience?” Sam ducked into the passenger’s side a split second before Dean could swat him across the back of the head.

Dean rounded the front of the Impala. Just before climbing in, he looked back at the trees, expecting to see the ghostly vision of the Headless Horseman once more.

Only still, silent woods met his gaze.

He shook his head, scooted behind the steering wheel, and gunned the engine. Whatever reason the Horseman had for watching Sammy go down on him, one thing remained certain—tonight was definitely one for the books.

**Author's Note:**

> Hope you enjoyed it!


End file.
